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In the title mol­ecule, C15H10N2O5S, there are weak C-H...O and C-H...N interactions which generate rings of motifs S(5), S(6), S(8), R21(5), R21(6), R12(4), R22(6), R22(7), R22(8) and R22(13). The supramolecular aggregation is completed by the presence of [pi]-[pi] interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803018166/ci6262sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803018166/ci6262Isup2.hkl
Contains datablock I

CCDC reference: 222901

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.038
  • wR factor = 0.078
  • Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.97
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for O6 - N3 = 5.09 su
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Aromatic sulfonates are used in monitoring the merging of lipids (Yachi et al., 1989), studying membrane fusion during acrosome reaction (Spungin et al., 1992), in the development of immunoaffinity chromatography for the purification of human coagulation factor (Tharakan et al., 1992), in chemical studies of viruses (Alford et al., 1991), in the development of technology for linking photosensitizers to model monoclonal antibodies (Jiang et al., 1990) and in the chemical modification of σ sub-units of E. coli RNA polymerase (Narayanan & Krakow, 1983). The molecular and crystal structure of 3-nitrobenzenesulfonyl chloride has recently been reported (Vembu Nallu Spencer & Howard, 2003c). An X-ray study of the title compound, (I), has now been undertaken in view of the biological importance of its analogues, and also to compare its structural parameters with those of its precursor, 3-nitrobenzenesulfonyl chloride.

A displacement ellipsoid plot of the two independent molecules of (I) is shown in Fig. 1 and selected geometric parameters are given in Table 1. The dihedral angles between the mean planes of the 3-nitrobenzene moiety and the quinoline rings are 8.28 (5) and 5.18 (5)° in molecules 1 and 2, respectively. This near-coplanar orientation is similar to that found in related aromatic sulfonates (Vembu Nallu Garrison Hindi & Youngs, 2003 Query; Vembu Nallu Garrison & Youngs, 2003a), and is in contrast with the non-coplanar orientation reported for similar compounds (Vembu Nallu Garrison & Youngs, 2003b,c,e,f; Vembu Nallu Spencer & Howard, 2003a,b). The crystal structure of (I) is stabilized by weak C—H···O and C—H···N interactions (Table 2). The range of H···O distances found in (I) agrees with that found for weak C—H···O bonds (Desiraju & Steiner, 1999).

As shown in Fig. 2, each C2—H2···O2, C2—H2···O3, C4—H4···O4, C6—H6···O1, C17—H17···O7, C17—H17···O10, C19—H19···O9 and C21—H21···O6 interaction generates rings of graph-set motif S(5) (Etter, 1990; Bernstein et al., 1995). The C2—H2···N2, C2—H2···O2 and C2—H2···O3 interactions constitute a set of heteroatomic trifurcated donor bonds, and the C17—H17···N4, C17—H17···O7 and C17—H17···O10 interactions constitute another set of heteroatomic trifurcated donor bonds. The C25—H25···O3 and C27—H27···O3 interactions constitute a pair of bifurcated acceptor bonds generating an S(6) motif. Each C2—H2···N2 and C17—H17···N4 interaction generates rings of graph-set motif S(8).

As can be seen in Fig. 3, the C4—H4···O8i and C5—H5···O9i interactions generate a sulfonyl fork motif of graph set R22(7). The C9—H9···O6iii and C8—H8···N3iii interactions generate an R22(6) motif. The C9—H9···O6iii and C8—H8···O6iii interactions constitute a pair of bifurcated acceptor bonds generating an R21(5) motif. The C9—H9···O6iii and C8—H8···O7iii interactions generate a nitro fork motif of graph set R22(7). The C8—H8···O6iii and C8—H8···O7iii interactions constitute a pair of bifurcated donor bonds generating a three-centred hydrogen-bonded chelate motif of graph set R12(4) (Vembu Nallu Garrison Hindi & Youngs, 2003 Query; Vembu Nallu Garrison & Youngs, 2003b,c,d,e,f,g; Vembu Nallu Spencer & Howard, 2003a,b,d,e). The C8—H8···N3iii, C8—H8···O6iii and C8—H8···O7iii interactions together constitute a set of heteroatomic trifurcated donor bonds. The C9—H9···O10iv and C10—H10···N4iv interactions together generate an R22(8) ring motif. The C10—H10···O8v and C12—H12···O8v interactions constitute a pair of bifurcated acceptor bonds generating an R21(6) motif. The C12—H12···O4vi and C13—H13···O3vi interactions generate a sulfonyl fork motif of graph set R22(7). The C24—H24···O1vii and C23—H23···O2vii interactions generate a nitro fork motif of graph set R22(7). The C14—H14···O9vii and C13—H13···O9vii interactions constitute a pair of bifurcated acceptor bonds forming an R21(5) motif. The C28—H28···O8xi and C25—H25···O7xi interactions together generate an R22(13) ring motif. There are several other C—H···O interactions which contribute to the supramolecular aggregation of the structure (Table 2) [symmetry codes: ?].

In the crystal structure (Fig. 4), there are five pairs of ππ interactions, with separations of 3.604 (1), 3.450 (1), 3.786 (1), 3.596 (1) and 3.781 (1) Å between Cg1 and Cg5(1 − x, y − 1/2, 3/2 − z), Cg2 and Cg2(1 − x, 1 − y, 1 − z), Cg2 and Cg3, Cg3 and Cg6, and Cg4 and Cg5(2 − x, y − 1/2, 3/2 − z), respectively, where Cg1, Cg2, Cg3, Cg4, Cg5 and Cg6 are the centroids of the rings formed by the atoms N2/C11—C15, N4/C26—C30, C1—C6, C7—C11/C15, C16—C21,and C22—C26/C30, respectively (Spek, 1998).

Experimental top

3-Nitrobenzenesulfonyl chloride (5 mmol) was dissolved in acetone (5 ml) and added to 8-hydroxyquinoline (5 mmol), which had been dissolved in NaOH (4 ml, 5%). The precipitate, (I) (5 mmol, yield 60%), was recrystallized from ethyl acetate.

Refinement top

All H atoms were located from difference Fourier maps and their positional parameters were refined. The isotropic displacement parameter of H28 was refined freely, but that of the others were set to 20% greater than their bonded partners. The C—H bond lengths are in the range 0.90 (2)–0.99 (2) Å. Reflections were measured to θmax = 27.16° with 97% completeness, but the data are 100% complete to 25°.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The structure of the two independent molecules of (I), showing 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Hydrogen bonds 1–12 (the numbers relate to the sequence of entries in Table 2).
[Figure 3] Fig. 3. Hydrogen bonds 14–16, 18, 23, 24, 31, 32, 33, 34 and 35 (the numbers relate to the sequence of entries in Table 2). Symmetry codes are as in Table 2.
[Figure 4] Fig. 4. Packing of the molecules in the unit cell of (I), viewed along the c axis, showing the ππ interactions.
8-Quinolyl 3-nitrobenzenesulfonate top
Crystal data top
C15H10N2O5SF(000) = 1360
Mr = 330.31Dx = 1.614 Mg m3
Monoclinic, P21/cMelting point = 429–431 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 8.6001 (6) ÅCell parameters from 2947 reflections
b = 23.0681 (16) Åθ = 3.0–26.6°
c = 13.9192 (9) ŵ = 0.27 mm1
β = 100.132 (2)°T = 120 K
V = 2718.3 (3) Å3Block, colourless
Z = 80.20 × 0.19 × 0.11 mm
Data collection top
Bruker Proteum M
diffractometer
4101 reflections with I > 2σ(I)
Radiation source: Bede microsourceRint = 0.050
Graphite monochromatorθmax = 27.2°, θmin = 2.3°
Detector resolution: 8 pixels mm-1h = 1011
ω scansk = 2928
18512 measured reflectionsl = 1715
6011 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: difference Fourier map
wR(F2) = 0.078Only H-atom coordinates refined
S = 0.90 w = 1/[σ2(Fo2) + (0.0308P)2]
where P = (Fo2 + 2Fc2)/3
6011 reflections(Δ/σ)max = 0.001
475 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
C15H10N2O5SV = 2718.3 (3) Å3
Mr = 330.31Z = 8
Monoclinic, P21/cMo Kα radiation
a = 8.6001 (6) ŵ = 0.27 mm1
b = 23.0681 (16) ÅT = 120 K
c = 13.9192 (9) Å0.20 × 0.19 × 0.11 mm
β = 100.132 (2)°
Data collection top
Bruker Proteum M
diffractometer
4101 reflections with I > 2σ(I)
18512 measured reflectionsRint = 0.050
6011 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.078Only H-atom coordinates refined
S = 0.90Δρmax = 0.29 e Å3
6011 reflectionsΔρmin = 0.36 e Å3
475 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.8324 (2)0.51014 (9)0.90468 (13)0.0196 (4)
C20.8705 (2)0.45883 (9)0.86385 (14)0.0186 (4)
H20.842 (2)0.4228 (9)0.8887 (13)0.022*
C30.9590 (2)0.46250 (8)0.78987 (13)0.0162 (4)
C41.0103 (2)0.51547 (9)0.75948 (14)0.0195 (4)
H41.074 (2)0.5176 (8)0.7093 (14)0.023*
C50.9710 (2)0.56585 (9)0.80393 (15)0.0225 (5)
H51.007 (2)0.6027 (9)0.7842 (14)0.027*
C60.8800 (2)0.56381 (9)0.87640 (15)0.0230 (5)
H60.849 (2)0.5988 (9)0.9076 (14)0.028*
C71.1130 (2)0.30928 (8)0.83009 (13)0.0158 (4)
C81.1749 (2)0.27127 (9)0.77273 (14)0.0183 (4)
H81.225 (2)0.2844 (8)0.7211 (14)0.022*
C91.1678 (2)0.21149 (9)0.79134 (15)0.0206 (4)
H91.209 (2)0.1853 (9)0.7486 (14)0.025*
C101.0995 (2)0.19208 (9)0.86662 (14)0.0198 (4)
H101.097 (2)0.1512 (9)0.8802 (14)0.024*
C111.0341 (2)0.23112 (8)0.92675 (13)0.0177 (4)
C120.9632 (2)0.21327 (9)1.00636 (14)0.0212 (5)
H120.962 (2)0.1735 (9)1.0228 (14)0.025*
C130.9016 (2)0.25390 (9)1.05974 (14)0.0224 (5)
H130.852 (2)0.2427 (8)1.1148 (15)0.027*
C140.9088 (2)0.31264 (9)1.03393 (14)0.0204 (4)
H140.862 (2)0.3419 (9)1.0721 (14)0.025*
C151.0388 (2)0.29166 (8)0.90828 (13)0.0160 (4)
S10.99733 (6)0.39803 (2)0.73114 (3)0.01685 (11)
N10.7359 (2)0.50669 (8)0.98294 (12)0.0273 (4)
N20.97490 (19)0.33219 (7)0.96164 (11)0.0183 (4)
O10.69341 (19)0.55219 (7)1.01525 (11)0.0413 (4)
O20.7048 (2)0.45857 (7)1.01087 (11)0.0412 (4)
O30.86002 (15)0.36216 (5)0.71618 (9)0.0207 (3)
O41.07176 (16)0.41200 (6)0.65044 (9)0.0247 (3)
O51.12583 (15)0.36961 (5)0.81393 (9)0.0181 (3)
C160.5212 (2)0.75457 (9)0.52266 (13)0.0186 (4)
C170.4825 (2)0.70577 (9)0.57011 (14)0.0182 (4)
H170.508 (2)0.6677 (9)0.5512 (13)0.022*
C180.4096 (2)0.71392 (8)0.65044 (13)0.0171 (4)
C190.3763 (2)0.76901 (9)0.68144 (14)0.0202 (4)
H190.325 (2)0.7731 (8)0.7342 (15)0.024*
C200.4171 (2)0.81680 (9)0.63120 (15)0.0231 (5)
H200.395 (2)0.8548 (9)0.6522 (14)0.028*
C210.4916 (2)0.81022 (9)0.55136 (15)0.0213 (4)
H210.516 (2)0.8424 (9)0.5159 (14)0.026*
C220.5123 (2)0.55864 (8)0.72292 (14)0.0171 (4)
C230.4424 (2)0.52216 (9)0.77916 (14)0.0206 (4)
H230.386 (2)0.5382 (8)0.8298 (14)0.025*
C240.4464 (2)0.46202 (9)0.76322 (15)0.0230 (5)
H240.394 (2)0.4369 (9)0.8024 (14)0.028*
C250.5221 (2)0.43991 (9)0.69351 (15)0.0216 (4)
H250.524 (2)0.3995 (9)0.6817 (14)0.026*
C260.5992 (2)0.47709 (8)0.63620 (13)0.0178 (4)
C270.6815 (2)0.45716 (9)0.56300 (14)0.0217 (5)
H270.682 (2)0.4165 (9)0.5523 (14)0.026*
C280.7513 (2)0.49593 (9)0.51009 (14)0.0227 (5)
H280.804 (2)0.4846 (9)0.4623 (15)0.027*
C290.7367 (2)0.55531 (9)0.52844 (14)0.0214 (5)
H290.779 (2)0.5827 (9)0.4876 (14)0.026*
C300.5937 (2)0.53792 (8)0.64962 (13)0.0161 (4)
S20.34832 (6)0.65290 (2)0.70999 (4)0.01902 (12)
N30.5998 (2)0.74681 (8)0.43752 (12)0.0237 (4)
N40.66102 (18)0.57689 (7)0.59520 (11)0.0190 (4)
O60.65727 (17)0.78946 (6)0.40500 (10)0.0311 (4)
O70.60271 (19)0.69770 (6)0.40374 (10)0.0350 (4)
O80.24357 (15)0.61813 (6)0.64254 (10)0.0254 (3)
O90.30028 (17)0.67150 (6)0.79759 (10)0.0293 (4)
O100.51163 (14)0.61914 (5)0.73848 (9)0.0189 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0166 (10)0.0277 (11)0.0147 (10)0.0004 (9)0.0030 (8)0.0025 (8)
C20.0194 (11)0.0192 (11)0.0170 (10)0.0007 (8)0.0024 (8)0.0008 (8)
C30.0158 (10)0.0157 (10)0.0163 (10)0.0009 (8)0.0007 (8)0.0005 (7)
C40.0184 (11)0.0214 (11)0.0188 (11)0.0019 (8)0.0033 (9)0.0014 (8)
C50.0230 (11)0.0173 (11)0.0259 (12)0.0027 (9)0.0006 (9)0.0015 (8)
C60.0215 (11)0.0203 (11)0.0256 (12)0.0016 (9)0.0005 (9)0.0048 (9)
C70.0138 (10)0.0149 (10)0.0174 (10)0.0005 (8)0.0012 (8)0.0021 (7)
C80.0147 (10)0.0249 (11)0.0156 (10)0.0012 (8)0.0035 (8)0.0008 (8)
C90.0171 (10)0.0233 (11)0.0212 (11)0.0044 (9)0.0029 (9)0.0046 (8)
C100.0173 (10)0.0161 (11)0.0250 (11)0.0018 (8)0.0009 (9)0.0009 (8)
C110.0145 (10)0.0218 (11)0.0159 (10)0.0010 (8)0.0002 (8)0.0016 (8)
C120.0204 (11)0.0222 (11)0.0194 (11)0.0025 (9)0.0006 (9)0.0047 (8)
C130.0204 (11)0.0314 (13)0.0153 (11)0.0036 (9)0.0034 (9)0.0030 (8)
C140.0179 (11)0.0259 (12)0.0176 (11)0.0002 (9)0.0033 (9)0.0041 (8)
C150.0123 (10)0.0186 (10)0.0159 (10)0.0005 (8)0.0007 (8)0.0006 (8)
S10.0196 (3)0.0161 (2)0.0154 (2)0.0003 (2)0.0046 (2)0.00009 (19)
N10.0248 (10)0.0360 (12)0.0221 (10)0.0012 (8)0.0069 (8)0.0053 (8)
N20.0190 (9)0.0197 (9)0.0163 (9)0.0012 (7)0.0033 (7)0.0032 (6)
O10.0437 (10)0.0423 (10)0.0434 (10)0.0002 (8)0.0232 (8)0.0198 (8)
O20.0535 (11)0.0398 (10)0.0383 (10)0.0051 (8)0.0302 (9)0.0076 (8)
O30.0193 (7)0.0185 (7)0.0226 (8)0.0010 (6)0.0007 (6)0.0012 (6)
O40.0338 (9)0.0232 (8)0.0199 (8)0.0018 (6)0.0127 (7)0.0017 (6)
O50.0182 (7)0.0155 (7)0.0205 (7)0.0009 (6)0.0025 (6)0.0021 (5)
C160.0172 (10)0.0239 (11)0.0147 (10)0.0008 (8)0.0032 (8)0.0009 (8)
C170.0165 (10)0.0178 (10)0.0199 (11)0.0011 (8)0.0022 (8)0.0028 (8)
C180.0154 (10)0.0185 (10)0.0169 (10)0.0012 (8)0.0017 (8)0.0006 (8)
C190.0184 (11)0.0248 (11)0.0178 (11)0.0034 (9)0.0041 (9)0.0015 (8)
C200.0226 (11)0.0187 (11)0.0265 (12)0.0041 (9)0.0005 (9)0.0031 (9)
C210.0209 (11)0.0186 (11)0.0234 (11)0.0006 (9)0.0011 (9)0.0036 (8)
C220.0146 (10)0.0165 (10)0.0190 (10)0.0003 (8)0.0001 (8)0.0005 (8)
C230.0162 (10)0.0277 (12)0.0183 (11)0.0015 (9)0.0042 (9)0.0025 (8)
C240.0177 (11)0.0236 (12)0.0271 (12)0.0021 (9)0.0024 (9)0.0098 (9)
C250.0214 (11)0.0146 (10)0.0267 (12)0.0009 (9)0.0017 (9)0.0032 (8)
C260.0158 (10)0.0186 (10)0.0168 (10)0.0004 (8)0.0032 (8)0.0007 (8)
C270.0217 (11)0.0213 (11)0.0197 (11)0.0036 (9)0.0030 (9)0.0034 (8)
C280.0226 (11)0.0309 (13)0.0142 (10)0.0032 (9)0.0018 (9)0.0042 (9)
C290.0223 (11)0.0247 (12)0.0174 (11)0.0026 (9)0.0039 (9)0.0009 (8)
C300.0142 (10)0.0187 (10)0.0144 (10)0.0019 (8)0.0002 (8)0.0008 (7)
S20.0182 (3)0.0189 (3)0.0218 (3)0.0008 (2)0.0087 (2)0.00012 (19)
N30.0207 (10)0.0301 (11)0.0208 (9)0.0015 (8)0.0048 (8)0.0024 (7)
N40.0185 (9)0.0214 (9)0.0173 (9)0.0018 (7)0.0040 (7)0.0008 (7)
O60.0331 (9)0.0293 (9)0.0342 (9)0.0006 (7)0.0152 (7)0.0101 (7)
O70.0513 (11)0.0298 (9)0.0295 (9)0.0055 (8)0.0228 (8)0.0085 (7)
O80.0190 (8)0.0217 (8)0.0340 (9)0.0009 (6)0.0008 (7)0.0006 (6)
O90.0367 (9)0.0273 (8)0.0295 (8)0.0044 (7)0.0211 (7)0.0010 (6)
O100.0175 (7)0.0176 (7)0.0217 (7)0.0011 (6)0.0038 (6)0.0012 (5)
Geometric parameters (Å, º) top
C1—C21.377 (3)C16—C171.376 (3)
C1—C61.383 (3)C16—C211.381 (3)
C1—N11.483 (2)C16—N31.475 (2)
C2—C31.387 (3)C17—C181.388 (3)
C2—H20.949 (19)C17—H170.953 (19)
C3—C41.390 (3)C18—C191.388 (3)
C3—S11.7560 (18)C18—S21.7606 (19)
C4—C51.386 (3)C19—C201.383 (3)
C4—H40.960 (19)C19—H190.926 (19)
C5—C61.382 (3)C20—C211.385 (3)
C5—H50.96 (2)C20—H200.95 (2)
C6—H60.98 (2)C21—H210.93 (2)
C7—C81.356 (3)C22—C231.359 (3)
C7—C151.415 (2)C22—O101.413 (2)
C7—O51.417 (2)C22—C301.418 (2)
C8—C91.407 (3)C23—C241.406 (3)
C8—H80.952 (19)C23—H230.993 (19)
C9—C101.363 (3)C24—C251.359 (3)
C9—H90.961 (19)C24—H240.96 (2)
C10—C111.412 (3)C25—C261.413 (3)
C10—H100.963 (19)C25—H250.95 (2)
C11—C121.416 (3)C26—C271.415 (3)
C11—C151.422 (3)C26—C301.418 (3)
C12—C131.360 (3)C27—C281.363 (3)
C12—H120.94 (2)C27—H270.95 (2)
C13—C141.406 (3)C28—C291.403 (3)
C13—H130.98 (2)C28—H280.91 (2)
C14—N21.319 (2)C29—N41.322 (2)
C14—H140.99 (2)C29—H290.96 (2)
C15—N21.368 (2)C30—N41.368 (2)
S1—O41.4242 (13)S2—O91.4208 (14)
S1—O31.4270 (13)S2—O81.4278 (14)
S1—O51.5909 (13)S2—O101.5938 (13)
N1—O21.221 (2)N3—O61.223 (2)
N1—O11.223 (2)N3—O71.228 (2)
C2—C1—C6123.24 (18)C17—C16—C21123.30 (18)
C2—C1—N1117.47 (17)C17—C16—N3118.07 (17)
C6—C1—N1119.29 (17)C21—C16—N3118.62 (17)
C1—C2—C3117.09 (18)C16—C17—C18117.26 (18)
C1—C2—H2120.3 (11)C16—C17—H17122.2 (11)
C3—C2—H2122.5 (11)C18—C17—H17120.4 (11)
C2—C3—C4121.66 (18)C17—C18—C19121.45 (18)
C2—C3—S1117.81 (14)C17—C18—S2119.07 (14)
C4—C3—S1120.46 (14)C19—C18—S2119.38 (14)
C5—C4—C3119.05 (18)C20—C19—C18119.21 (19)
C5—C4—H4119.8 (12)C20—C19—H19121.2 (12)
C3—C4—H4121.1 (12)C18—C19—H19119.6 (12)
C6—C5—C4120.74 (19)C19—C20—C21120.83 (19)
C6—C5—H5119.4 (12)C19—C20—H20119.8 (12)
C4—C5—H5119.9 (12)C21—C20—H20119.4 (12)
C5—C6—C1118.19 (18)C16—C21—C20117.94 (18)
C5—C6—H6122.1 (12)C16—C21—H21121.1 (12)
C1—C6—H6119.7 (12)C20—C21—H21120.8 (12)
C8—C7—C15122.96 (18)C23—C22—O10120.60 (17)
C8—C7—O5119.46 (16)C23—C22—C30122.02 (18)
C15—C7—O5117.55 (16)O10—C22—C30117.33 (16)
C7—C8—C9119.43 (18)C22—C23—C24119.60 (18)
C7—C8—H8121.2 (11)C22—C23—H23119.9 (11)
C9—C8—H8119.4 (11)C24—C23—H23120.5 (11)
C10—C9—C8120.13 (18)C25—C24—C23120.73 (18)
C10—C9—H9121.9 (12)C25—C24—H24120.6 (12)
C8—C9—H9118.0 (12)C23—C24—H24118.6 (12)
C9—C10—C11121.09 (18)C24—C25—C26120.42 (19)
C9—C10—H10119.9 (12)C24—C25—H25121.4 (12)
C11—C10—H10119.0 (12)C26—C25—H25118.2 (12)
C10—C11—C12123.33 (18)C25—C26—C27123.55 (18)
C10—C11—C15119.49 (17)C25—C26—C30119.78 (17)
C12—C11—C15117.18 (17)C27—C26—C30116.66 (17)
C13—C12—C11119.32 (19)C28—C27—C26119.94 (19)
C13—C12—H12121.0 (12)C28—C27—H27123.3 (12)
C11—C12—H12119.7 (12)C26—C27—H27116.8 (12)
C12—C13—C14119.04 (18)C27—C28—C29118.70 (19)
C12—C13—H13120.8 (12)C27—C28—H28122.1 (13)
C14—C13—H13120.1 (12)C29—C28—H28119.1 (13)
N2—C14—C13124.66 (18)N4—C29—C28124.50 (18)
N2—C14—H14116.7 (12)N4—C29—H29116.9 (12)
C13—C14—H14118.6 (11)C28—C29—H29118.5 (12)
N2—C15—C7119.99 (17)N4—C30—C26123.40 (16)
N2—C15—C11123.11 (16)N4—C30—C22119.18 (17)
C7—C15—C11116.89 (16)C26—C30—C22117.41 (16)
O4—S1—O3119.43 (8)O9—S2—O8119.27 (9)
O4—S1—O5108.26 (8)O9—S2—O10108.09 (8)
O3—S1—O5108.56 (7)O8—S2—O10108.40 (8)
O4—S1—C3108.84 (9)O9—S2—C18108.59 (9)
O3—S1—C3109.91 (8)O8—S2—C18110.24 (9)
O5—S1—C3100.09 (8)O10—S2—C18100.62 (8)
O2—N1—O1124.52 (17)O6—N3—O7124.29 (17)
O2—N1—C1117.70 (17)O6—N3—C16118.15 (17)
O1—N1—C1117.78 (18)O7—N3—C16117.55 (16)
C14—N2—C15116.65 (17)C29—N4—C30116.77 (17)
C7—O5—S1117.13 (11)C22—O10—S2118.15 (11)
C6—C1—C2—C31.0 (3)C21—C16—C17—C180.2 (3)
N1—C1—C2—C3179.20 (17)N3—C16—C17—C18179.58 (17)
C1—C2—C3—C41.4 (3)C16—C17—C18—C190.3 (3)
C1—C2—C3—S1175.74 (15)C16—C17—C18—S2176.78 (15)
C2—C3—C4—C50.4 (3)C17—C18—C19—C200.1 (3)
S1—C3—C4—C5176.64 (15)S2—C18—C19—C20176.57 (15)
C3—C4—C5—C61.0 (3)C18—C19—C20—C210.6 (3)
C4—C5—C6—C11.4 (3)C17—C16—C21—C200.9 (3)
C2—C1—C6—C50.4 (3)N3—C16—C21—C20179.70 (18)
N1—C1—C6—C5179.42 (18)C19—C20—C21—C161.1 (3)
C15—C7—C8—C90.8 (3)O10—C22—C23—C24179.12 (17)
O5—C7—C8—C9177.42 (17)C30—C22—C23—C241.7 (3)
C7—C8—C9—C100.2 (3)C22—C23—C24—C251.3 (3)
C8—C9—C10—C110.4 (3)C23—C24—C25—C260.4 (3)
C9—C10—C11—C12179.4 (2)C24—C25—C26—C27179.42 (19)
C9—C10—C11—C150.3 (3)C24—C25—C26—C301.8 (3)
C10—C11—C12—C13179.28 (19)C25—C26—C27—C28179.26 (19)
C15—C11—C12—C131.1 (3)C30—C26—C27—C280.4 (3)
C11—C12—C13—C140.5 (3)C26—C27—C28—C291.3 (3)
C12—C13—C14—N21.4 (3)C27—C28—C29—N41.0 (3)
C8—C7—C15—N2178.20 (18)C25—C26—C30—N4177.95 (18)
O5—C7—C15—N23.6 (3)C27—C26—C30—N40.9 (3)
C8—C7—C15—C111.4 (3)C25—C26—C30—C221.4 (3)
O5—C7—C15—C11176.83 (16)C27—C26—C30—C22179.76 (17)
C10—C11—C15—N2178.47 (18)C23—C22—C30—N4179.72 (18)
C12—C11—C15—N21.9 (3)O10—C22—C30—N42.8 (3)
C10—C11—C15—C71.1 (3)C23—C22—C30—C260.4 (3)
C12—C11—C15—C7178.56 (18)O10—C22—C30—C26177.87 (16)
C2—C3—S1—O4172.80 (15)C17—C18—S2—O9171.09 (16)
C4—C3—S1—O44.39 (19)C19—C18—S2—O912.39 (19)
C2—C3—S1—O340.29 (18)C17—C18—S2—O856.56 (18)
C4—C3—S1—O3136.90 (16)C19—C18—S2—O8119.96 (16)
C2—C3—S1—O573.81 (16)C17—C18—S2—O1057.73 (17)
C4—C3—S1—O5109.00 (16)C19—C18—S2—O10125.75 (16)
C2—C1—N1—O24.7 (3)C17—C16—N3—O6168.33 (18)
C6—C1—N1—O2175.12 (19)C21—C16—N3—O611.1 (3)
C2—C1—N1—O1175.54 (19)C17—C16—N3—O711.9 (3)
C6—C1—N1—O14.7 (3)C21—C16—N3—O7168.74 (19)
C13—C14—N2—C150.7 (3)C28—C29—N4—C300.3 (3)
C7—C15—N2—C14179.44 (18)C26—C30—N4—C291.3 (3)
C11—C15—N2—C141.0 (3)C22—C30—N4—C29179.44 (17)
C8—C7—O5—S183.34 (19)C23—C22—O10—S270.4 (2)
C15—C7—O5—S198.37 (17)C30—C22—O10—S2112.05 (16)
O4—S1—O5—C7108.12 (13)O9—S2—O10—C22110.47 (13)
O3—S1—O5—C722.91 (14)O8—S2—O10—C2220.12 (14)
C3—S1—O5—C7138.04 (13)C18—S2—O10—C22135.79 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···N20.949 (19)2.51 (2)3.281 (3)138.2 (15)
C2—H2···O20.949 (19)2.379 (18)2.691 (2)98.7 (13)
C2—H2···O30.949 (19)2.808 (18)3.023 (2)93.8 (12)
C4—H4···O40.960 (19)2.568 (19)2.926 (2)102.3 (13)
C6—H6···O10.98 (2)2.427 (19)2.734 (2)97.6 (13)
C17—H17···N40.953 (19)2.49 (2)3.336 (3)147.5 (15)
C17—H17···O70.953 (19)2.437 (18)2.704 (2)95.7 (13)
C17—H17···O100.953 (19)2.833 (18)3.056 (2)94.3 (12)
C19—H19···O90.926 (19)2.527 (19)2.911 (2)105.3 (14)
C21—H21···O60.93 (2)2.45 (2)2.726 (2)96.7 (14)
C25—H25···O30.95 (2)2.968 (19)3.382 (2)107.9 (14)
C27—H27···O30.95 (2)2.809 (19)3.249 (2)109.2 (14)
C4—H4···O8i0.960 (19)2.977 (19)3.665 (2)129.7 (14)
C5—H5···O9i0.96 (2)2.96 (2)3.749 (3)140.3 (15)
C6—H6···N2ii0.98 (2)2.68 (2)3.377 (3)128.7 (15)
C9—H9···O6iii0.961 (19)2.661 (19)3.344 (2)128.4 (15)
C8—H8···N3iii0.952 (19)2.970 (19)3.807 (2)147.4 (14)
C8—H8···O6iii0.952 (19)2.761 (19)3.380 (2)123.4 (14)
C8—H8···O7iii0.952 (19)2.506 (19)3.444 (2)168.3 (16)
C29—H29···O4iii0.96 (2)2.496 (19)3.305 (2)141.8 (16)
C9—H9···O10iv0.961 (19)2.82 (2)3.566 (2)134.9 (15)
C10—H10···N4iv0.963 (19)2.67 (2)3.346 (2)127.7 (15)
C10—H10···O8v0.963 (19)2.99 (2)3.391 (2)106.5 (13)
C12—H12···O8v0.94 (2)2.94 (2)3.313 (2)105.3 (14)
C12—H12···O4vi0.94 (2)2.71 (2)3.547 (2)147.9 (16)
C13—H13···O3vi0.98 (2)2.79 (2)3.509 (2)130.6 (15)
C24—H24···O1vii0.96 (2)2.78 (2)3.517 (3)133.9 (15)
C14—H14···O9vii0.99 (2)2.492 (19)3.217 (2)129.9 (15)
C13—H13···O9vii0.98 (2)2.77 (2)3.336 (2)117.5 (14)
C23—H23···O2vii0.993 (19)2.479 (19)3.412 (2)156.3 (15)
C19—H19···O3viii0.926 (19)2.76 (2)3.435 (2)130.6 (15)
C21—H21···O1ix0.93 (2)2.87 (2)3.694 (3)147.3 (16)
C24—H24···O5x0.96 (2)2.81 (2)3.651 (2)146.7 (16)
C28—H28···O8xi0.91 (2)2.78 (2)3.387 (2)125.9 (16)
C25—H25···O7xi0.95 (2)2.68 (2)3.543 (3)151.7 (16)
Symmetry codes: (i) x+1, y, z; (ii) x+2, y+1, z+2; (iii) x+2, y+1, z+1; (iv) x+2, y1/2, z+3/2; (v) x+1, y1/2, z+3/2; (vi) x, y+1/2, z+1/2; (vii) x+1, y+1, z+2; (viii) x+1, y+1/2, z+3/2; (ix) x, y+3/2, z1/2; (x) x1, y, z; (xi) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC15H10N2O5S
Mr330.31
Crystal system, space groupMonoclinic, P21/c
Temperature (K)120
a, b, c (Å)8.6001 (6), 23.0681 (16), 13.9192 (9)
β (°) 100.132 (2)
V3)2718.3 (3)
Z8
Radiation typeMo Kα
µ (mm1)0.27
Crystal size (mm)0.20 × 0.19 × 0.11
Data collection
DiffractometerBruker Proteum M
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
18512, 6011, 4101
Rint0.050
(sin θ/λ)max1)0.642
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.078, 0.90
No. of reflections6011
No. of parameters475
H-atom treatmentOnly H-atom coordinates refined
Δρmax, Δρmin (e Å3)0.29, 0.36

Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1998), SHELXTL (Sheldrick, 1998), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···N20.949 (19)2.51 (2)3.281 (3)138.2 (15)
C2—H2···O20.949 (19)2.379 (18)2.691 (2)98.7 (13)
C2—H2···O30.949 (19)2.808 (18)3.023 (2)93.8 (12)
C4—H4···O40.960 (19)2.568 (19)2.926 (2)102.3 (13)
C6—H6···O10.98 (2)2.427 (19)2.734 (2)97.6 (13)
C17—H17···N40.953 (19)2.49 (2)3.336 (3)147.5 (15)
C17—H17···O70.953 (19)2.437 (18)2.704 (2)95.7 (13)
C17—H17···O100.953 (19)2.833 (18)3.056 (2)94.3 (12)
C19—H19···O90.926 (19)2.527 (19)2.911 (2)105.3 (14)
C21—H21···O60.93 (2)2.45 (2)2.726 (2)96.7 (14)
C25—H25···O30.95 (2)2.968 (19)3.382 (2)107.9 (14)
C27—H27···O30.95 (2)2.809 (19)3.249 (2)109.2 (14)
C4—H4···O8i0.960 (19)2.977 (19)3.665 (2)129.7 (14)
C5—H5···O9i0.96 (2)2.96 (2)3.749 (3)140.3 (15)
C6—H6···N2ii0.98 (2)2.68 (2)3.377 (3)128.7 (15)
C9—H9···O6iii0.961 (19)2.661 (19)3.344 (2)128.4 (15)
C8—H8···N3iii0.952 (19)2.970 (19)3.807 (2)147.4 (14)
C8—H8···O6iii0.952 (19)2.761 (19)3.380 (2)123.4 (14)
C8—H8···O7iii0.952 (19)2.506 (19)3.444 (2)168.3 (16)
C29—H29···O4iii0.96 (2)2.496 (19)3.305 (2)141.8 (16)
C9—H9···O10iv0.961 (19)2.82 (2)3.566 (2)134.9 (15)
C10—H10···N4iv0.963 (19)2.67 (2)3.346 (2)127.7 (15)
C10—H10···O8v0.963 (19)2.99 (2)3.391 (2)106.5 (13)
C12—H12···O8v0.94 (2)2.94 (2)3.313 (2)105.3 (14)
C12—H12···O4vi0.94 (2)2.71 (2)3.547 (2)147.9 (16)
C13—H13···O3vi0.98 (2)2.79 (2)3.509 (2)130.6 (15)
C24—H24···O1vii0.96 (2)2.78 (2)3.517 (3)133.9 (15)
C14—H14···O9vii0.99 (2)2.492 (19)3.217 (2)129.9 (15)
C13—H13···O9vii0.98 (2)2.77 (2)3.336 (2)117.5 (14)
C23—H23···O2vii0.993 (19)2.479 (19)3.412 (2)156.3 (15)
C19—H19···O3viii0.926 (19)2.76 (2)3.435 (2)130.6 (15)
C21—H21···O1ix0.93 (2)2.87 (2)3.694 (3)147.3 (16)
C24—H24···O5x0.96 (2)2.81 (2)3.651 (2)146.7 (16)
C28—H28···O8xi0.91 (2)2.78 (2)3.387 (2)125.9 (16)
C25—H25···O7xi0.95 (2)2.68 (2)3.543 (3)151.7 (16)
Symmetry codes: (i) x+1, y, z; (ii) x+2, y+1, z+2; (iii) x+2, y+1, z+1; (iv) x+2, y1/2, z+3/2; (v) x+1, y1/2, z+3/2; (vi) x, y+1/2, z+1/2; (vii) x+1, y+1, z+2; (viii) x+1, y+1/2, z+3/2; (ix) x, y+3/2, z1/2; (x) x1, y, z; (xi) x+1, y+1, z+1.
 

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